Semiconductor photoresist composition and method of forming pattern using the same

Abstract

Disclosed are a semiconductor photoresist composition and a method of forming a pattern using the same, the semiconductor photoresist composition including a tin-containing organometallic compound, a compound represented by Chemical Formula 1, and a solvent.

Description

[0001] Cross-reference to related applications

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2024-0022098, filed in the Korean Intellectual Property Office on February 15, 2024, the entire contents of which are incorporated herein by reference. Technical Field

[0003] Embodiments of the present disclosure relate to semiconductor photoresist compositions and methods of forming patterns using the same. Background Art

[0004] Extreme ultraviolet (EUV) lithography is gaining attention as a technology for manufacturing next-generation semiconductor devices. EUV lithography is a patterning technique that uses EUV radiation with a wavelength of 13.5 nanometers as an exposure light source. EUV lithography enables the formation of extremely fine patterns (e.g., less than or equal to 20 nanometers) during the exposure process during semiconductor device manufacturing.

[0005] Extreme ultraviolet (EUV) lithography is enabled by the development of compatible photoresists that can perform at spatial resolutions of 16 nanometers or less. Currently, efforts are underway to meet the insufficient specifications of chemically amplified (CA) photoresists for next-generation devices, such as resolution, photospeed, and feature roughness (also known as line edge roughness or LER).

[0006] Intrinsic image blurring due to acid-catalyzed reactions in these polymer-based resists limits resolution of small feature sizes, a problem that has long existed in electron-beam (e-beam) lithography. Chemically amplified (CA) resists are designed for high sensitivity, but they can have greater difficulties with EUV exposure, in part because their elemental composition reduces the resist's light absorption at 13.5 nm, thereby reducing their sensitivity.

[0007] Chemically amplified photoresists can have difficulty with small feature sizes due to roughness issues, and the line edge roughness (LER) of chemically amplified photoresists has been experimentally shown to increase as photospeed decreases due in part to the nature of the acid catalyst process. Therefore, due to these drawbacks and issues with CA photoresists, a new high-performance photoresist is needed in the semiconductor industry.

[0008] To overcome the aforementioned shortcomings of chemically amplified (CA) organic photosensitive compositions, inorganic photosensitive compositions have been studied. These compositions are primarily used for negative-tone patterns that are resistant to removal by developer compositions due to chemical modification via a non-chemical amplification mechanism. Inorganic compositions contain inorganic elements with higher EUV absorptivity than hydrocarbon groups, ensuring sensitivity via a non-chemical amplification mechanism. Furthermore, they are less sensitive to stochastic effects, resulting in low line-edge roughness and a relatively low number of defects.

[0009] Inorganic photoresists based on tungsten peroxypolyacids mixed with tungsten, niobium, titanium, and / or tantalum have been reported as radiation-sensitive materials for patterning.

[0010] These materials are effective for large-pitch patterning of bilayer configurations as extreme ultraviolet (deep UV), X-ray, and electron beam sources. Recently, if cationic hafnium metal oxide sulfate (HfSO x ) materials with a peroxide complexing agent for use with projected EUV exposure images at 15 nm half-pitch (HP), then impressive performance has been achieved. The system exhibits the highest performance of non-CA photoresists and has practical photospeeds approaching suitable levels for EUV photoresists. However, hafnium metal oxide sulfate materials with peroxide complexing agents have some practical disadvantages. First, these materials are coated in a corrosive sulfuric acid / hydrogen peroxide mixture and have insufficient shelf life stability. Second, structural changes to improve performance as a composite mixture are not easy to make. Third, development should be carried out in a very highly concentrated 25 wt% tetramethylammonium hydroxide (TMAH) solution and / or the like.

[0011] Recently, research has been actively underway on tin-containing molecules with excellent extreme ultraviolet (EUV) absorption. In organotin polymers, alkyl ligands dissociate through light absorption or the resulting secondary electrons, crosslinking adjacent chains via oxobond bonds. This enables negative patterning that is indelible with organic developers. While these organotin polymers exhibit greatly improved sensitivity while maintaining resolution and line-edge roughness, further improvements in patterning properties are required for commercial viability. Summary of the Invention

[0012] Some embodiments of the present disclosure provide a semiconductor photoresist composition having excellent sensitivity and exposure latitude (EL) characteristics.

[0013] Some embodiments provide a method of forming a pattern using a semiconductor photoresist composition.

[0014] A semiconductor photoresist composition according to some embodiments includes a tin-containing organometallic compound; a compound represented by Chemical Formula 1; and a solvent.

[0015] Methods of forming patterns according to some embodiments include providing an etch target layer on a substrate, coating a semiconductor photoresist composition on the etch target layer to form a photoresist layer, patterning the photoresist layer to form a photoresist pattern, and etching the etch target layer using the photoresist pattern as an etch mask.

[0016] The semiconductor photoresist composition according to some embodiments may achieve excellent sensitivity and exposure latitude (EL) characteristics. BRIEF DESCRIPTION OF THE DRAWINGS

[0017] The drawings, together with the specification, illustrate embodiments of the presently disclosed subject matter, and, together with the description, serve to explain principles of the embodiments of the presently disclosed subject matter.

[0018] Figure 1A-1E is a cross-sectional view illustrating a method of forming a pattern using a semiconductor photoresist composition according to some embodiments of the present disclosure.

[0019] Explanation of Figure Numbers

[0020] 100: substrate;

[0021] 102: Film;

[0022] 104: resist bottom layer;

[0023] 106: photoresist layer;

[0024] 106a: unexposed area;

[0025] 106b: exposure area;

[0026] 108: photoresist pattern;

[0027] 110: patterned mask;

[0028] 112: organic layer pattern;

[0029] 114: Thin film pattern. DETAILED DESCRIPTION

[0030] Hereinafter, embodiments are described in more detail with reference to the accompanying drawings. In the following description of the present disclosure, some functions and / or configurations may be omitted to clarify the subject matter of the present disclosure.

[0031] In order to clearly illustrate the subject matter of the present disclosure, certain descriptions and relationships may be omitted, and the same or similar configuration elements are represented by the same reference numerals throughout the disclosure. In addition, for better understanding and ease of description, the size and thickness of each configuration shown in the drawings may be arbitrarily shown, and the present disclosure is not necessarily limited thereto.

[0032] In the drawings, the thickness of layers, films, panels, regions, etc. may be exaggerated for clarity. In the drawings, the thickness of some layers or regions may be exaggerated for clarity. It will be understood that if an element such as a layer, film, region, or substrate is referred to as being "on" another element, it can be directly on the other element or intervening elements may also be present.

[0033] As used herein, "substituted" refers to the replacement of a hydrogen atom by a deuterium, a halogen, a hydroxyl group, a thiol group, a cyano group, a nitro group, -NRR' (wherein R and R' are each independently hydrogen, a substituted or unsubstituted C1-C30 saturated or unsaturated aliphatic hydrocarbon group, a substituted or unsubstituted C3-C30 saturated or unsaturated alicyclic hydrocarbon group, or a substituted or unsubstituted C6 to C30 aromatic hydrocarbon group), -SiRR'R" (wherein R, R' and R" are each independently The term "alkyl" refers to a group consisting of a hydrogen atom, a substituted or unsubstituted C1-C30 saturated or unsaturated aliphatic hydrocarbon group, a substituted or unsubstituted C3 to C30 saturated or unsaturated alicyclic hydrocarbon group, a substituted or unsubstituted C6 to C30 aromatic hydrocarbon group, a C1 to C30 alkyl group, a C1 to C10 haloalkyl group, a C1 to C10 alkylsilyl group, a C3 to C30 cycloalkyl group, a C6 to C30 aryl group, a C1 to C20 alkoxy group, a C1 to C20 sulfide group, or a combination thereof. "Unsubstituted" means that a hydrogen atom is not replaced by another substituent and the hydrogen atom remains.

[0034] As used herein, unless otherwise defined, "alkyl" refers to a straight-chain or branched aliphatic hydrocarbon group. The alkyl group may be a "saturated alkyl group" without any double or triple bonds.

[0035] The alkyl group may be a C1 to C8 alkyl group. For example, the alkyl group may be a C1 to C7 alkyl group, a C1 to C6 alkyl group, or a C1 to C5 alkyl group. For example, the C1 to C5 alkyl group may be a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, or a 2,2-dimethylpropyl group.

[0036] As used herein, unless otherwise defined, "cycloalkyl" refers to a monovalent cyclic aliphatic hydrocarbon group.

[0037] The cycloalkyl group may be a C3 to C8 cycloalkyl group, a C3 to C7 cycloalkyl group, or a C3 to C6 cycloalkyl group. For example, the cycloalkyl group may be a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, but is not limited thereto.

[0038] As used herein, "aliphatic unsaturated organic group" refers to a hydrocarbon group containing bonds wherein the bonds between carbon atoms in the molecule are double bonds, triple bonds, or a combination thereof.

[0039] The aliphatic unsaturated organic group can be a C2 to C8 aliphatic unsaturated organic group.For example, the aliphatic unsaturated organic group can be a C2 to C7 aliphatic unsaturated organic group, a C2 to C6 aliphatic unsaturated organic group, a C2 to C5 aliphatic unsaturated organic group or a C2 to C4 aliphatic unsaturated organic group.For example, the C2 to C4 aliphatic unsaturated organic group can be vinyl, ethynyl, allyl, 1-propenyl, 1-methyl isophthalic acid-propenyl, 2-propenyl, 2-methyl-2-propenyl, 1-propynyl, 1-methyl-1-propynyl, 2-propynyl, 2-methyl-2-propynyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-butynyl, 2-butynyl or 3-butynyl.

[0040] As used herein, "aryl" means that all atoms in a cyclic substituent have p orbitals and that the p orbitals are conjugated and can include monocyclic functional groups, polycyclic functional groups, or fused (eg, rings that share adjacent pairs of carbon atoms) functional groups.

[0041] As used herein, "heteroaryl" may refer to an aryl group that includes at least one heteroatom selected from N, O, S, P, and Si. Two or more heteroaryl groups may be directly linked by a sigma bond, or if the heteroaryl group includes two or more rings, the two or more rings may be fused together. If the heteroaryl group is a fused ring, each ring may include one to three heteroatoms.

[0042] As used herein, unless otherwise defined, "alkenyl" refers to an aliphatically unsaturated alkenyl group containing at least one double bond as a straight-chain or branched aliphatic hydrocarbon group.

[0043] As used herein, unless otherwise defined, "alkynyl" refers to an aliphatically unsaturated alkynyl group containing at least one triple bond as a straight-chain or branched aliphatic hydrocarbon radical.

[0044] Hereinafter, semiconductor photoresist compositions according to some embodiments are described.

[0045] A semiconductor photoresist composition according to some embodiments includes a tin-containing organometallic compound, a compound represented by Chemical Formula 1; and a solvent.

[0046] Chemical formula 1

[0047]

[0048] In Chemical Formula 1,

[0049] L 1is a single bond (e.g., a single covalent bond) or a substituted or unsubstituted C1-C10 alkylene group, and

[0050] R 1 is a substituted or unsubstituted C2 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C7 to C30 aralkyl group, -L a -X a (where X 1 It is O or S, L a is a single bond (eg, a single covalent bond) or a substituted or unsubstituted C1 to C20 alkylene group, and R a is a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C30 aryl group), or -L b -N(R b )(R c )(where L b is a single bond (eg, a single covalent bond) or a substituted or unsubstituted C1 to C20 alkylene group, and R b and R c are each independently hydrogen or a substituted or unsubstituted C1 to C20 alkyl group).

[0051] A semiconductor photoresist composition has improved sensitivity and LER as well as excellent resolution by including a branched carboxylic acid-based compound having a hydroxyl functional group.

[0052] In an embodiment, if R 1 If the alkyl group is an alkyl group, the exposure latitude (EL) characteristics can be further improved by including a carbon chain having two or more carbon atoms.

[0053] For example, R 1 It may be a substituted or unsubstituted C2 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C7 to C30 aralkyl group, or -L a -X a (where X 1 It is O or S, L a is a single bond or a substituted or unsubstituted C1 to C20 alkylene group, and R a is a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C30 aryl group).

[0054] As an example, R1 It may be ethyl, propyl, butyl, isopropyl, tert-butyl, 2,2-dimethylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, vinyl, propenyl, butenyl, ethynyl, propynyl, butynyl, phenyl, tolyl, xylyl, benzyl, ethoxy or propoxy.

[0055] As an example, the compound represented by Chemical Formula 1 may be one selected from the compounds listed in Group 1.

[0056] Group 1

[0057]

[0058] The compound represented by Chemical Formula 1 may be included in an amount of about 0.01 wt % to about 10 wt % based on 100 wt % of the semiconductor photoresist composition.

[0059] For example, the compound represented by Chemical Formula 1 may be included in an amount of about 0.01 wt % to about 5 wt % or about 0.05 wt % to about 5 wt % based on 100 wt % of the semiconductor photoresist composition.

[0060] The tin-containing organometallic compound may be included in an amount of about 0.5 wt % to about 30 wt % based on 100 wt % of the semiconductor photoresist composition.

[0061] The semiconductor photoresist composition according to some embodiments may improve the sensitivity of the photoresist by including the tin-containing organometallic compound and the compound represented by Chemical Formula 1 within the above content range.

[0062] The semiconductor photoresist composition according to some embodiments may include the tin-containing organometallic compound and the compound represented by Chemical Formula 1 in a weight ratio of about 99.9:0.1 to about 80:20. For example, the semiconductor photoresist composition may include the tin-containing organometallic compound and the compound represented by Chemical Formula 1 in a weight ratio of about 95:5 to about 85:15.

[0063] If the weight ratio of the tin-containing organometallic compound and the compound represented by Chemical Formula 1 satisfies the above range, a semiconductor photoresist composition having excellent sensitivity may be provided.

[0064] The tin-containing organometallic compound may include at least one selected from an organooxy group and an organocarbonyloxy group.

[0065] The tin-containing organometallic compound can be represented by Chemical Formula 2.

[0066] Chemical formula 2

[0067]

[0068] In Chemical Formula 2,

[0069] R 2 is selected from substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, and substituted or unsubstituted C7 to C30 aralkyl,

[0070] R 3 to R 5 are each independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C7 to C30 aralkyl group, an alkoxy group, and an aryloxy group (-OR d ), where R d is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof), a carboxyl group (-O(CO)R e , where R e is hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof), an alkylamide or dialkylamide group (—NR f R g , where R f and R g are each independently hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkene, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof), an amide group (-NR h (COR i , where R h and R i are each independently hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof), an amidino group (-NR j C(NR k )Rl , where R j 、R k and R l , substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof), alkylthio, and arylthiol (-SR m , where R m , substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof) or thiocarbonyl (-S(CO)R n , R n is hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof, and

[0071] Selected from R 3 to R 5 At least one of alkoxy and aryloxy (-OR d , where R d is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof), a carboxyl group (-O(C=O)R e , where R e is hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof), an alkylamide or a dialkylamide (-NR f R g , where R f and R g are each independently hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof), an amide group (-NR h (COR i )), where R hand R i are each independently hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof), amidino (-NR j C(NR k )R l , where R j 、R k and R l each independently hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof), alkylthio, and arylthiol (-SR m , where R m is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof), and a thiocarbonyl group (-S(C=O)R n , where R n is hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof).

[0072] In some embodiments, selected from R 3 to R 5 At least one of them may be selected from alkoxy and aryloxy (-OR d , where R d is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof) and a carboxyl group (-O(C=O)R e , where R e is hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof).

[0073] In an embodiment, the compound represented by Chemical Formula 2 comprises -OR d or -OC(=O)R e As a ligand, a pattern formed using a semiconductor photoresist composition containing the ligand can exhibit excellent limiting resolution.

[0074] In an embodiment, -OR d or -OC(=O)R e The ligand may determine the solubility of the compound represented by Chemical Formula 2 in a solvent.

[0075] R 2 may be a substituted or unsubstituted C1 to C8 alkyl group, a substituted or unsubstituted C3 to C8 cycloalkyl group, a substituted or unsubstituted C2 to C8 aliphatic unsaturated organic group including one or more double bonds and / or triple bonds, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C4 to C20 heteroaryl group, a carbonyl group, an ethoxy group, a propoxy group, or a combination thereof,

[0076] R d may be a substituted or unsubstituted C1 to C8 alkyl group, a substituted or unsubstituted C3 to C8 cycloalkyl group, a substituted or unsubstituted C2 to C8 alkenyl group, a substituted or unsubstituted C2 to C8 alkynyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof, and

[0077] R e It can be hydrogen, substituted or unsubstituted C1 to C8 alkyl, substituted or unsubstituted C3 to C8 cycloalkyl, substituted or unsubstituted C2 to C8 alkenyl, substituted or unsubstituted C2 to C8 alkynyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof.

[0078] R 2 can be methyl, ethyl, propyl, butyl, isopropyl, tert-butyl, 2,2-dimethylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, vinyl, propenyl, butenyl, ethynyl, propynyl, butynyl, phenyl, tolyl, xylyl, benzyl, formyl, acetyl, propionyl, butyryl, valeryl, ethoxy, propoxy, or a combination thereof,

[0079] R d It can be ethyl, propyl, butyl, isopropyl, tert-butyl, 2,2-dimethylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, vinyl, propenyl, butenyl, ethynyl, propynyl, butynyl, phenyl, tolyl, xylyl, benzyl or a combination thereof,

[0080] R eIt may be hydrogen, ethyl, propyl, butyl, isopropyl, tert-butyl, 2,2-dimethylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, vinyl, propenyl, butenyl, ethynyl, propynyl, butynyl, phenyl, tolyl, xylyl, benzyl or a combination thereof.

[0081] In an embodiment, the organotin compound may be represented by Chemical Formula 3 or Chemical Formula 4.

[0082] Chemical Formula 3

[0083] R 6 z SnO (2-(z / 2)-(x / 2)) (OH) x

[0084] In Chemical Formula 3,

[0085] R 6 is a C1 to C31 hydrocarbon group, 0 < z ≤ 2, and 0 < (z + x) ≤ 4;

[0086] Chemical Formula 4

[0087] R 7 n Sn m X l Y k

[0088] Wherein, in Chemical Formula 4,

[0089] R 7 is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C2 to C20 aliphatic unsaturated organic group including one or more double bonds and / or triple bonds, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C4 to C30 heteroaryl group, a carbonyl group, an oxiranyl group, an oxetanyl group or a combination thereof,

[0090] X is sulfur (S), selenium (Se) or tellurium (Te),

[0091] Y is -OR o or -OC(=O)R p ,

[0092] Where R o is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group or a combination thereof,

[0093] R pis hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof, and

[0094] n, m, l and k are each independently an integer from 1 to 20.

[0095] The solvent of the semiconductor photoresist composition according to some embodiments may be an organic solvent, and may be, for example, an aromatic compound (e.g., xylene, toluene, etc.), an alcohol (e.g., 4-methyl-2-pentenol, 4-methyl-2-propanol, 1-butanol, methanol, isopropanol, 1-propanol, etc.), an ether (e.g., anisole, tetrahydrofuran, etc.), an ester (n-butyl acetate, propylene glycol monomethyl ether acetate, ethyl acetate, ethyl lactate, etc.), a ketone (e.g., methyl ethyl ketone, 2-heptanone, etc.), or a mixture thereof, but is not limited thereto.

[0096] The semiconductor photoresist composition according to some embodiments may further include a resin in addition to the above-mentioned tin-containing organometallic compound, the compound represented by Chemical Formula 1, and a solvent.

[0097] The resin may be a phenolic resin comprising at least one aromatic moiety of Group 2.

[0098] Group 2

[0099]

[0100] The resin may have a weight average molecular weight of about 500 to about 20,000.

[0101] The resin may be included in an amount of about 0.1 wt % to about 50 wt % based on the total amount of the semiconductor photoresist composition.

[0102] If the resin is included in the above content range, excellent etching resistance and heat resistance may be achieved.

[0103] In an embodiment, a semiconductor photoresist composition according to some embodiments may be composed of the aforementioned tin-containing organometallic compound, a compound represented by Chemical Formula 1, a solvent, and a resin.

[0104] However, the semiconductor photoresist composition according to the aforementioned embodiment may further include additives as needed or desired. Examples of the additives may be surfactants, crosslinking agents, leveling agents, organic acids, quenchers, or combinations thereof.

[0105] The surfactant may include, for example, alkylbenzene sulfonate, alkylpyridinium salt, polyethylene glycol, quaternary ammonium salt, or a combination thereof, but is not limited thereto.

[0106] The crosslinking agent may be, for example, a melamine-based crosslinking agent, a substituted urea-based crosslinking agent, an acrylic crosslinking agent, an epoxy-based crosslinking agent, and / or a polymer-based crosslinking agent, but is not limited thereto. It may be a crosslinking agent having at least two crosslinking-forming substituents, for example, compounds such as methoxymethylated glycoluril, butoxymethylated glycoluril, methoxymethylated melamine, butoxymethylated melamine, methoxymethylated benzoguanamine, butoxymethylated benzoguanamine, 4-hydroxybutyl acrylate, urethane acrylate, 1,4-butylene glycol diglycidyl methacrylate, glycidyl alcohol, 1,2-cyclohexanedicarboxylic acid diglycidyl ether, trimethylpropane triglycidyl ether, 1,3-bis(glycidyloxypropyl)tetramethyldisiloxane, methoxymethylated urea, butoxymethylated urea, methoxymethylated thiourea, and the like.

[0107] A leveling agent may be used to improve coating flatness during printing and may be any suitable commercially available leveling agent.

[0108] The organic acid may include p-toluenesulfonic acid, benzenesulfonic acid, p-dodecylbenzenesulfonic acid, 1,4-naphthalene disulfonic acid, methanesulfonic acid, sulfonium fluoride salt, malonic acid, citric acid, propionic acid, methacrylic acid, oxalic acid, lactic acid, glycolic acid, succinic acid, or a combination thereof, but is not limited thereto.

[0109] The quencher can be diphenyl(p-tolyl)amine, methyldiphenylamine, triphenylamine, phenylenediamine, naphthylamine, diaminonaphthalene, or a combination thereof.

[0110] In some embodiments, an acid compound other than the compound represented by Chemical Formula 1 may be additionally mixed with the semiconductor photoresist composition of the present disclosure.

[0111] The amount of additives used can be controlled according to the appropriate or desired properties.

[0112] In an embodiment, the semiconductor photoresist composition may further include a silane coupling agent as an adhesion enhancer to improve the close contact force with the substrate (for example, to improve the adhesion of the semiconductor photoresist composition to the substrate). The silane coupling agent can be, for example, a silane compound containing a carbon-carbon unsaturated bond such as vinyltrimethoxysilane, vinyltriethoxysilane, vinyltrichlorosilane, vinyltris(β-methoxyethoxy)silane; and / or 3-methacryloxypropyltrimethoxysilane, 3-acryloxypropyltrimethoxysilane, p-phenylyltrimethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane; trimethoxy[3-(phenylamino)propyl]silane, etc., but is not limited thereto.

[0113] The semiconductor photoresist composition can be formed into a pattern with a high aspect ratio without collapse. Therefore, in order to form a fine pattern with a width of, for example, about 5 nanometers to about 100 nanometers, for example, about 5 nanometers to about 80 nanometers, for example, about 5 nanometers to about 70 nanometers, for example, about 5 nanometers to about 50 nanometers, for example, about 5 nanometers to about 40 nanometers, for example, about 5 nanometers to about 30 nanometers, or for example, about 5 nanometers to about 20 nanometers, the semiconductor photoresist composition can be used for a photolithography process using light with a wavelength in the range of about 5 nanometers to about 150 nanometers, for example, about 5 nanometers to about 100 nanometers, about 5 nanometers to about 80 nanometers, about 5 nanometers to about 50 nanometers, about 5 nanometers to about 30 nanometers, or about 5 nanometers to about 20 nanometers. Therefore, the semiconductor photoresist composition according to some embodiments can be used to realize extreme ultraviolet lithography using EUV light with a wavelength of about 13.5 nanometers.

[0114] According to some embodiments, a method for forming a pattern using the aforementioned semiconductor photoresist composition is provided. For example, the pattern formed can be a photoresist pattern.

[0115] Methods of forming patterns according to some embodiments include providing an etch target layer on a substrate, coating a semiconductor photoresist composition on the etch target layer to form a photoresist layer, patterning the photoresist layer to form a photoresist pattern, and etching the etch target layer using the photoresist pattern as an etch mask.

[0116] In the following, reference Figure 1A-1E Methods for forming patterns using semiconductor photoresist compositions are described. Figure 1A-1E is a cross-sectional view illustrating a method of forming a pattern using a semiconductor photoresist composition according to some embodiments.

[0117] refer to Figure 1A An object to be etched is prepared. The object to be etched may be a thin film 102 on a semiconductor substrate 100. Hereinafter, the object to be etched is defined as the thin film 102. The surface of the thin film 102 is cleaned to remove impurities and the like remaining thereon. The thin film 102 may be, for example, a silicon nitride layer, a polysilicon layer, and / or a silicon oxide layer.

[0118] Subsequently, a resist base layer composition for forming the resist base layer 104 is spin-coated on the surface of the cleaned thin film 102. However, the embodiment is not limited thereto, and various suitable coating methods such as spray coating, dip coating, knife-edge coating, printing methods (such as inkjet printing and / or screen printing), etc. may be used.

[0119] The process of applying the resist underlayer may be omitted. Hereinafter, a process including applying the resist underlayer will be described.

[0120] Then, the applied composition is dried and baked to form a resist bottom layer 104 on the thin film 102. The baking may be performed at about 100°C to about 500°C (eg, about 100°C to about 300°C).

[0121] The resist bottom layer 104 is formed between the substrate 100 and the photoresist layer 106 and can therefore prevent or reduce unevenness in the photoresist line width and a reduction in pattern formability that would otherwise occur if light reflected from the interface between the substrate 100 and the photoresist layer 106 and / or the hard mask between the layers were scattered into unintended photoresist areas.

[0122] refer to Figure 1B The photoresist layer 106 is formed by coating a semiconductor photoresist composition on the resist base layer 104. The photoresist layer 106 is obtained by coating the semiconductor photoresist composition on the thin film 102 formed on the substrate 100 and then curing it by heat treatment.

[0123] In an embodiment, forming a pattern using the semiconductor photoresist composition may include coating the semiconductor photoresist composition on the substrate 100 having the thin film 102 by spin coating, slit coating, inkjet printing, etc., and then drying it to form the photoresist layer 106 .

[0124] The semiconductor photoresist composition has been shown in detail, and a description thereof may not be repeated below.

[0125] Subsequently, a first baking process is performed on the substrate 100 having the photoresist layer 106. The first baking process may be performed at a temperature of about 80°C to about 120°C.

[0126] refer to Figure 1C , the photoresist layer 106 may be selectively exposed using a patterned mask 110 .

[0127] For example, exposure can use activating radiation including light having a high-energy wavelength, such as EUV (extreme ultraviolet; wavelength of about 13.5 nanometers), electron beam (E-Beam) and / or the like, as well as light having a short wavelength, such as i-line (wavelength of about 365 nanometers), KrF excimer laser (wavelength of about 248 nanometers), ArF excimer laser (wavelength of about 193 nanometers) and / or the like.

[0128] In embodiments, exposure light according to some embodiments may have a short wavelength range of about 5 nm to about 150 nm and a high energy wavelength, such as EUV (extreme ultraviolet; wavelength 13.5 nm), electron beam (E-Beam), and / or the like.

[0129] The exposed region 106 b of the photoresist layer 106 has a different solubility from the unexposed region 106 a of the photoresist layer 106 due to a polymer formed by a cross-linking reaction (eg, condensation reaction) between the organometallic compounds.

[0130] Subsequently, a second baking process is performed on the substrate 100. The second baking process may be performed at a temperature of about 90° C. to about 200° C. Due to the second baking process, the exposed region 106 b of the photoresist layer 106 easily becomes insoluble in a developer.

[0131] exist Figure 1D In the process, the developer is used to dissolve and remove the unexposed area 106a of the photoresist layer to form a photoresist pattern 108. In an embodiment, the unexposed area 106a of the photoresist layer is dissolved and removed using an organic solvent such as 2-heptanone and / or the like to complete the photoresist pattern 108 corresponding to the negative image.

[0132] As described above, the developer used in the pattern forming method according to some embodiments may be an organic solvent. The organic solvent used in the pattern forming method according to some embodiments may be, for example, a ketone such as methyl ethyl ketone, acetone, cyclohexanone, 2-heptanone, etc.; an alcohol such as 4-methyl-2-propanol, 1-butanol, isopropanol, 1-propanol, methanol, etc.; an ester such as propylene glycol monomethyl ether acetate, ethyl acetate, ethyl lactate, n-butyl acetate, butyrolactone, etc.; an aromatic compound such as benzene, xylene, toluene, etc., or a combination thereof.

[0133] However, the photoresist pattern according to some embodiments is not necessarily limited to a negative image, but can be formed to have a positive image. In an embodiment, the developer for forming the positive image can be a quaternary ammonium hydroxide composition, such as tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, or a combination thereof.

[0134] As described above, exposure to light having high energy, such as extreme ultraviolet (EUV; wavelength of 13.5 nm), E-beam (electron beam), and light having a wavelength, such as i-line (wavelength of approximately 365 nm), KrF excimer laser (wavelength of approximately 248 nm), ArF excimer laser (wavelength of approximately 193 nm), can provide the photoresist pattern 108 having a width of approximately 5 nm to approximately 100 nm. For example, the photoresist pattern 108 may have a thickness of approximately 5 nm to approximately 90 nm, approximately 5 nm to approximately 80 nm, approximately 5 nm to approximately 70 nm, approximately 5 nm to approximately 60 nm, approximately 5 nm to approximately 50 nm, approximately 5 nm to approximately 40 nm, approximately 5 nm to approximately 30 nm, or approximately 5 nm to approximately 20 nm.

[0135] In an embodiment, the photoresist pattern 108 may have a pitch with a half pitch less than or equal to about 50 nanometers (e.g., less than or equal to about 40 nanometers, e.g., less than or equal to about 30 nanometers, e.g., less than or equal to about 20 nanometers, or e.g., less than or equal to about 15 nanometers) and a line width roughness less than or equal to about 10 nanometers, or less than or equal to about 5 nanometers, less than or equal to about 3 nanometers, or less than or equal to about 2 nanometers.

[0136] In an embodiment, the photoresist pattern 108 is used as an etching mask to etch the resist bottom layer 104. Through the etching process, an organic layer pattern 112 is formed. The organic layer pattern 112 may also have a width corresponding to the width of the photoresist pattern 108.

[0137] refer to Figure 1E The exposed thin film 102 is etched by using the photoresist pattern 108 as an etching mask. Thus, the thin film is formed into a thin film pattern 114.

[0138] The etching of the thin film 102 may be, for example, dry etching using an etching gas, and the etching gas may be, for example, CHF 3 , CF 4 , Cl 2 , BCl 3 and / or a mixed gas thereof.

[0139] In the exposure process, the width of the thin film pattern 114 formed by using the photoresist pattern 108 may correspond to the width of the photoresist pattern 108 formed by the exposure process using the EUV light source. For example, the thin film pattern 114 may have a width of about 5 nanometers to about 100 nanometers, which is equal to the width of the photoresist pattern 108. For example, the width of the thin film pattern 114 formed by using the photoresist pattern 108 may be about 5 nanometers to about 90 nanometers, about 5 nanometers to about 80 nanometers, about 5 nanometers to about 70 nanometers, about 5 nanometers to about 60 nanometers, about 5 nanometers to about 50 nanometers, about 5 nanometers to about 40 nanometers, about 5 nanometers to about 30 nanometers, or about 5 nanometers to about 20 nanometers, and more specifically, less than or equal to 20 nanometers, like the width of the photoresist pattern 108 formed by the exposure process using the EUV light source.

[0140] Hereinafter, the embodiments of the present disclosure will be described in more detail through the preparation examples of the aforementioned semiconductor photoresist composition. However, the present disclosure is not technically limited to the following embodiments.

[0141] Synthesis of organometallic compounds

[0142] Synthesis example 1

[0143] 40.7 g of t-butyltriphenyltin (t-butylSnPh 3 ) and 300 g of propionic acid were added to a 250 mL two-necked round-bottom flask, and then refluxed by heating for 24 hours.

[0144] The compound represented by Chemical Formula 5 is obtained by removing unreacted propionic acid therefrom under reduced pressure.

[0145] Chemical formula 5

[0146]

[0147] Synthesis example 2

[0148] 30 ml of anhydrous pentane was added to 10 g of tert-amyltin trichloride (t-AmylSnCl3) and the temperature was maintained at 0°C. 7.4 g of diethylamine and 6.1 g of ethanol were added thereto, followed by stirring at room temperature for 1 hour. When the reaction was complete, the resultant was filtered, concentrated, and vacuum-dried to obtain the compound represented by Chemical Formula 6.

[0149] Chemical formula 6

[0150]

[0151] Synthesis example 3

[0152] 10 g of dibutyltin dichloride was dissolved in 30 mL of ether, 70 mL of a 1 M sodium hydroxide (NaOH) aqueous solution was added, and the mixture was stirred for 1 hour. After stirring, the resulting solid was filtered, washed three times with 25 mL of deionized water, and dried under reduced pressure at 100° C. to obtain an organometallic compound represented by Chemical Formula 7 with a weight-average molecular weight of 1500.

[0153] Chemical formula 7

[0154]

[0155] Preparation of semiconductor photoresist compositions

[0156] Examples 1 to 11 and Comparative Examples 1 to 6

[0157] The compounds represented by Chemical Formulas 5 to 7 and the compounds represented by Chemical Formulas 8 to 10 according to Synthesis Examples 1 to 3 or lactic acid were dissolved in 4-methyl-2-pentanol at a concentration of 2 wt % at the weight ratios shown in Table 1, and then filtered with a 0.1 μm polytetrafluoroethylene (PTFE) syringe filter to prepare a semiconductor photoresist composition.

[0158]

[0159] Table 1

[0160]

[0161] Evaluation: Evaluation of sensitivity, line edge roughness (LER) and exposure latitude (EL)

[0162] Each of the photoresist compositions of the Examples and Comparative Examples was spin-coated at 1500 rpm for 30 seconds on a 200 mm circular silicon wafer with hexamethyldisilazane (HMDS) deposited on the surface, baked at 100° C. for 60 seconds (post-coating bake (PAB)), and then allowed to stand at room temperature (23±2° C.) for 30 seconds.

[0163] Subsequently, a linear array of 50 circular pads with a diameter of 500 microns was projected onto the wafer coated with each photoresist composition using EUV light (Lawrence Berkeley National Laboratory Micro Exposure Tool (MET)). The pad exposure time was adjusted so that an increasing EUV dose was applied to each pad.

[0164] Then, after exposure, the resist and substrate were baked on a hot plate at 160°C for 120 seconds. The baked film was developed in propylene glycol monomethyl ether acetate (PGMEA) solvent to form a negative image. Finally, the resulting film was baked again on a hot plate at 150°C for 2 minutes to complete the process.

[0165] Critical dimension-scanning electron microscopy (CD-SEM) was used to measure the effect of resist line width on exposure dose (energy) variations. The appropriate sensitivity for each exposure dose was confirmed using the resist line width that varied depending on the exposure dose, allowing the exposure latitude (EL) to be calculated according to Equation 1. Furthermore, after measuring LER from CD-SEM images, sensitivity, EL, and line edge roughness were evaluated according to the following criteria, and the results are shown in Table 2.

[0166] *Equation 1: EL = (E +10％ -E -10％ ) / Eop×100%

[0167] (Eop: optimal exposure dose for target CD, E +10％ 、E -10％ : Error range of exposure dose of target CD (±10%)

[0168] Sensitivity evaluation criteria

[0169] -A: less than 16mJ / cm 2

[0170] -B: greater than or equal to 16mJ / cm 2 and less than or equal to 18mJ / cm 2

[0171] -C: greater than 18mJ / cm 2

[0172] Evaluation criteria for LER

[0173] -○: Less than or equal to 3 nanometers

[0174] -△: greater than 3 nanometers and less than or equal to 6 nanometers

[0175] -X: larger than 6 nanometers

[0176] EL evaluation criteria

[0177] -A: greater than or equal to 20%

[0178] -B: greater than or equal to 10% and less than 20%

[0179] -C: greater than or equal to 5% and less than 10%

[0180] -D: less than or equal to 5%

[0181] Table 2

[0182]

[0183]

[0184] Referring to the results of Table 2, the patterns formed using the semiconductor photoresist compositions of Examples 1 to 11, respectively, exhibited superior sensitivity and LER and / or EL characteristics compared to the patterns formed using the semiconductor photoresist compositions of Comparative Examples 1 to 6, respectively.

[0185] In the above, certain embodiments have been described and illustrated. However, it will be apparent to those skilled in the art that the present disclosure is not limited to the embodiments as described, and that various modifications and variations may be made without departing from the spirit and scope of the present disclosure. Therefore, the modified or varied embodiments themselves may not depart from the technical ideas and aspects of the present disclosure, and the modified embodiments are within the scope of the appended claims and their equivalents.

Claims

1. A semiconductor photoresist composition comprising: Tin-containing organometallic compounds; A compound represented by Chemical Formula 1; and Solvent: Chemical formula 1 Wherein, in Chemical Formula 1, L 1 is a single bond or a substituted or unsubstituted C1 to C10 alkylene group, and R 1 is a substituted or unsubstituted C2 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C7 to C30 aralkyl group, -L a -X a or -L b -N(R b )(R c ), where X 1 It is O or S, L a is a single bond or a substituted or unsubstituted C1 to C20 alkylene group, R a is a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C30 aryl group, and wherein L b is a single bond or a substituted or unsubstituted C1 to C20 alkylene group, R b and R c Each is independently hydrogen or a substituted or unsubstituted C1 to C20 alkyl group.

2. The semiconductor photoresist composition according to claim 1, wherein: R 1 is ethyl, propyl, butyl, isopropyl, tert-butyl, 2,2-dimethylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, ethenyl, propenyl, butenyl, ethynyl, propynyl, butynyl, phenyl, tolyl, xylyl, benzyl, ethoxy or propoxy.

3. The semiconductor photoresist composition according to claim 1, wherein: The compound represented by Chemical Formula 1 is one selected from the compounds listed in Group 1: Group 1 4. The semiconductor photoresist composition according to claim 1, wherein: The compound represented by Chemical Formula 1 may be present in an amount of 0.01 wt % to 10 wt % based on 100 wt % of the semiconductor photoresist composition.

5. The semiconductor photoresist composition according to claim 1, wherein: The compound represented by Chemical Formula 1 may be present in an amount of 0.5 wt % to 5 wt % based on 100 wt % of the semiconductor photoresist composition.

6. The semiconductor photoresist composition according to claim 1, wherein: The content of the tin-containing organic metal compound is 0.5 wt % to 30 wt % based on 100 wt % of the semiconductor photoresist composition.

7. The semiconductor photoresist composition according to claim 1, wherein: The tin-containing organometallic compound and the compound represented by Chemical Formula 1 are included in a weight ratio of 99.9:0.1 to 80:

20.

8. The semiconductor photoresist composition according to claim 1, wherein: The semiconductor photoresist composition further includes an additive of a surfactant, a cross-linking agent, a leveler, an organic acid, a quencher, or a combination thereof.

9. The semiconductor photoresist composition according to claim 1, wherein: The tin-containing organometallic compound comprises at least one selected from the group consisting of an organooxy group and an organocarbonyloxy group.

10. The semiconductor photoresist composition according to claim 1, wherein: The tin-containing organometallic compound is represented by Chemical Formula 2: Chemical formula 2 Wherein, in Chemical Formula 2, R 2 is selected from substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, and substituted or unsubstituted C7 to C30 aralkyl, R 3 to R 5 Each is independently a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 alkenyl group; a substituted or unsubstituted C2 to C20 alkynyl group; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C7 to C30 aralkyl group; or d Alkyloxy and aryloxy represented by R d is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof; -O(CO)R e Represents a carboxyl group, where R e is hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof; -NR f R g An alkylamide or dialkylamide group, wherein R f and R g are each independently hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof; -NR h (COR i ) represents an amide group, wherein R h and R i are each independently hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof; -NR j C(NR k )R l represents an amidine group, wherein R j 、R k and R l are each independently hydrogen, substituted or unsubstituted C3 to C20 alkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof; -SR m Alkylthio and aromatic thiol represented by R m is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof; or is represented by -S(CO)R n represents a thiocarbonyl group, wherein R n is hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof, and Selected from R 3 to R 5 At least one of -OR d Alkyloxy and aryloxy represented by R d is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof; e Represents a carboxyl group, where R e is hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof; -NR f R g An alkylamide or dialkylamide group, wherein R f and R g are each independently hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof; -NR h (C=OR i ) represents an amide group, wherein R h and R i are each independently hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof; -NR j C(NR k )R l represents an amidine group, wherein R j 、R k and R l are each independently hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof; -SR m Alkylthio and aromatic thiol represented by R m is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof; and is represented by -S(C=O)R n represents a thiocarbonyl group, wherein R n is hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof.

11. The semiconductor photoresist composition according to claim 10, wherein: R 2 is a substituted or unsubstituted C1 to C8 alkyl group, a substituted or unsubstituted C3 to C8 cycloalkyl group, a substituted or unsubstituted C2 to C8 aliphatic unsaturated organic group including one or more double bonds and / or triple bonds, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C4 to C20 heteroaryl group, a carbonyl group, an ethoxy group, a propoxy group, or a combination thereof, R d is a substituted or unsubstituted C1 to C8 alkyl group, a substituted or unsubstituted C3 to C8 cycloalkyl group, a substituted or unsubstituted C2 to C8 alkenyl group, a substituted or unsubstituted C2 to C8 alkynyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof, and R e is hydrogen, substituted or unsubstituted C1 to C8 alkyl, substituted or unsubstituted C3 to C8 cycloalkyl, substituted or unsubstituted C2 to C8 alkenyl, substituted or unsubstituted C2 to C8 alkynyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof.

12. The semiconductor photoresist composition according to claim 1, wherein: The tin-containing organometallic compound is represented by Chemical Formula 3 or Chemical Formula 4: Chemical formula 3 R 6 z SnO (2-(z / 2)-(x / 2)) (OH) x Wherein, in Chemical Formula 3, R 6 is a C1 to C31 hydrocarbyl group, 0 < z ≤ 2, and 0 < (z + x) ≤ 4; Chemical formula 4 R 7 n Sn m X l Y k Wherein, in Chemical Formula 4, R 7 is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C2 to C20 aliphatic unsaturated organic group including one or more double bonds and / or triple bonds, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C4 to C30 heteroaryl group, a carbonyl group, an ethylene oxide group, a propylene oxide group, or a combination thereof, X is sulfur (S), selenium (Se) or tellurium (Te), Y is -OR o or -OC(=O)R p , where R o is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof, R p is hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof, and n, m, l and k are each independently an integer from 1 to 20.

13. A method for forming a pattern, comprising: providing an etching target layer on a substrate; coating the semiconductor photoresist composition according to any one of claims 1 to 12 on the etching target layer to form a photoresist layer; patterning the photoresist layer to form a photoresist pattern; and The etch target layer is etched using the photoresist pattern as an etch mask.

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